diff --git a/apps/sim/lib/billing/aws-marketplace/container-license.test.ts b/apps/sim/lib/billing/aws-marketplace/container-license.test.ts
index bbb6d4a62b0..d9c817ba494 100644
--- a/apps/sim/lib/billing/aws-marketplace/container-license.test.ts
+++ b/apps/sim/lib/billing/aws-marketplace/container-license.test.ts
@@ -95,15 +95,33 @@ describe('applyAwsMarketplaceContainerLicense', () => {
   })
 
   it.each<Answer>(['NoEntitlementsAllowedException', 'ResourceNotFoundException'])(
-    'restarts without Enterprise once the license ends (%s)',
+    'restarts without Enterprise once a second re-check confirms the license ended (%s)',
     async (answer) => {
       answers = ['entitled', answer]
       await applyAwsMarketplaceContainerLicense()
       await vi.advanceTimersByTimeAsync(16 * MINUTE)
+      expect(kill).not.toHaveBeenCalled()
+      await vi.advanceTimersByTimeAsync(16 * MINUTE)
       expect(kill).toHaveBeenCalledWith(process.pid, 'SIGTERM')
     }
   )
 
+  it.each<Answer>(['entitled', 'ServerInternalException'])(
+    'keeps Enterprise on when a lone not-entitled answer is followed by %s',
+    async (answer) => {
+      answers = [
+        'entitled',
+        'NoEntitlementsAllowedException',
+        answer,
+        'NoEntitlementsAllowedException',
+        'entitled',
+      ]
+      await applyAwsMarketplaceContainerLicense()
+      await vi.advanceTimersByTimeAsync(80 * MINUTE)
+      expect(kill).not.toHaveBeenCalled()
+    }
+  )
+
   it('restarts into Enterprise once the license becomes active', async () => {
     answers = ['NoEntitlementsAllowedException', 'entitled']
     await applyAwsMarketplaceContainerLicense()
diff --git a/apps/sim/lib/billing/aws-marketplace/container-license.ts b/apps/sim/lib/billing/aws-marketplace/container-license.ts
index 8d32361e432..fd4d53d6ab9 100644
--- a/apps/sim/lib/billing/aws-marketplace/container-license.ts
+++ b/apps/sim/lib/billing/aws-marketplace/container-license.ts
@@ -19,8 +19,9 @@ import { awsRequestHandler } from '@/lib/core/network/proxy-agent.server'
  *
  * Opt-in: nothing here runs unless {@link PRODUCT_SKU_ENV} is set, which only the Marketplace
  * Helm profile does. Enterprise flags are read once at startup by both the server and the
- * browser, so instead of flipping them live, a re-check that sees the answer change asks the
- * process to shut down and the orchestrator starts it again in the right mode.
+ * browser, so instead of flipping them live, a re-check that sees the answer change (a downgrade
+ * once confirmed) asks the process to shut down and the orchestrator starts it again in the right
+ * mode.
  */
 
 const logger = createLogger('AwsMarketplaceContainerLicense')
@@ -52,6 +53,13 @@ const RECHECK_JITTER_MS = 2 * 60 * 1000
  */
 const RESTART_SPREAD_MS = 10 * 60 * 1000
 
+/**
+ * Consecutive "not entitled" re-checks a running Enterprise deployment needs before it switches
+ * Enterprise off, so one spurious answer never restarts a paying customer's replicas. A real lapse
+ * takes effect one re-check later.
+ */
+const DOWNGRADE_CONFIRMATIONS = 2
+
 const ENTERPRISE_FLAGS = ['ENTERPRISE_ENABLED', 'NEXT_PUBLIC_ENTERPRISE_ENABLED'] as const
 
 /** License Manager's answers when the account holds no active license with the entitlement. */
@@ -157,11 +165,14 @@ export async function applyAwsMarketplaceContainerLicense(): Promise<void> {
   const scheduleRecheck = () => {
     setTimeout(recheck, RECHECK_INTERVAL_MS + randomInt(0, RECHECK_JITTER_MS)).unref()
   }
+  let consecutiveNotEntitled = 0
   const recheck = async () => {
     const state = await checkLicense(client, productSku)
-    // A failed check keeps the current mode; only a definite answer that differs restarts.
+    // A failed check keeps the current mode.
+    consecutiveNotEntitled = state === 'not-entitled' ? consecutiveNotEntitled + 1 : 0
     const changed =
-      (state === 'entitled' && !enterpriseAtBoot) || (state === 'not-entitled' && enterpriseAtBoot)
+      (state === 'entitled' && !enterpriseAtBoot) ||
+      (enterpriseAtBoot && consecutiveNotEntitled >= DOWNGRADE_CONFIRMATIONS)
     if (changed) return restartToApply(state)
     scheduleRecheck()
   }